Carbocupration-functionalization of arynes: rapid access to variably ortho-substituted ((E)-3-phenylprop-1-enyl)silanes.
A consecutive three-component coupling reaction involving a lithium di[3-(prop-1-enyltrimethylsilyl)]cuprate, variably substituted ortho-arynes, and a selection of common electrophiles is described. The method affords readily functionalized homobenzylic vinylsilanes with exceptional E-diastereoselectivity and allows for in situ incorporation of carbon- or heteroatom-based electrophiles into the arene.
Ganta
Ashok
A
Department of Chemistry, The University of Alabama, Box 870336, Tuscaloosa, Alabama 35487-0336, USA.
Snowden
Timothy S
TS
D003300:Copper / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D013997:Time Factors
D006841:Hydrocarbons, Aromatic; D009942:Organometallic Compounds; D012821:Silanes; D003300:Copper